CN101108858A - Method for preparing sulphuric acid cephalosporium quinol - Google Patents
Method for preparing sulphuric acid cephalosporium quinol Download PDFInfo
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- CN101108858A CN101108858A CNA2006100484240A CN200610048424A CN101108858A CN 101108858 A CN101108858 A CN 101108858A CN A2006100484240 A CNA2006100484240 A CN A2006100484240A CN 200610048424 A CN200610048424 A CN 200610048424A CN 101108858 A CN101108858 A CN 101108858A
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- sulphuric acid
- cephalosporium quinol
- extraction
- acid
- cefquinome
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Abstract
A method for preparing the cefquinome sulfate is provided, which adopts the cefotaxime acid as the raw material which reacts with the tetrahydroquinoline to gain the cefquinome; the active carbon reacts with the sulphuric acid in the ethanol solution after decolorization to gain the final product- cefquinome sulfate, namely, (6R-7R)-7-[(2-amino-4-thiazolyl)-( methoxyimino) acetylamino]-3-[(5, 6, 7, 8-tetrahydroquinoline)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]octyl-2-alkene-2-sulphate. The invention not only comprises the cefquinome but also has the advantage of directly serving for the animal health industry as the special antibiotics for the animals with broad spectrum, high efficiency, low toxin and low residual.
Description
Technical field:
The present invention relates to the veterinary drug preparation technical field, particularly a kind of method for preparing sulphuric acid cephalosporium quinol.
Background technology:
Cefquinome (Cefquinom), it is first animal specific the 4th generation cephalosporins, has a broad antifungal spectrum, anti-microbial activity is strong, it is strong to gram-positive microorganism usefulness for cephalosporin analog antibiotic to have overcome first three, to the relative more weak shortcoming of negative bacterium effect, Gram-negative bacteria, gram-positive microorganism, anerobe had broad-spectrum antibacterial activity; Its kinetic character is good, absorbs soon, and peak time is short, and bioavailability is higher, can reach higher tissue concentration at tissues such as lung, mammary gland; Cefquinome toxicity is low, and is residual less in the edible tissue of animal; The respiratory system infection and the mammitis of cow clinical treatment that are widely used in pig, ox.This medicine is safer, no carcinogenic, teratogenesis and embryotoxicity.Cefquinome is water insoluble, and making increases molten water-based after the salt, be convenient to clinical application, and hydroiodic acid HI Cefquinome character instability is difficult for preserving, and sulphuric acid cephalosporium quinol character is more stable, and convenient the preservation and transportation is convenient to make preparation again and is applicable to clinical application.
Summary of the invention:
Strong to gram-positive microorganism usefulness for cephalosporin analog antibiotic in order to have overcome first three, to the relative more weak shortcoming of negative bacterium effect, animal specific the 4th generation cephalosporins Cefquinome has absorption soon, and peak time is short, the characteristics that bioavailability is higher.Without hydroiodic acid HI, after the alkali extraction, directly produce sulphuric acid cephalosporium quinol behind cefotaxime acid and the side chain reaction generation Cefquinome with the sulfuric acid salify.Make the production technology innovation, improve product purity and reduce production costs, be beneficial to industrialized production.
In order to realize the foregoing invention purpose, the present invention adopts following technical scheme:
The described method for preparing sulphuric acid cephalosporium quinol, with the cefotaxime acid is the reaction of raw material and tetrahydroquinoline, after obtaining the product Cefquinome, through extraction, react in ethanolic soln with sulfuric acid behind the activated carbon decolorizing and obtain the final product sulphuric acid cephalosporium quinol, be i.e. (6R-7R)-7-[(2-amino-4-thiazolyl)-(methoxyimino) kharophen]-3-[(5,6,7, the 8-tetrahydric quinoline group) methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-vitriol;
Its chemical reaction equation process is:
Cefotaxime acid
Cefquinome
Sulphuric acid cephalosporium quinol
Its concrete technical process is: cefotaxime acid is through Cefquinome, select for use suitable alkaline solution to make extraction agent, extraction back directly with sulfuric acid synthesize sulphuric acid cephalosporium quinol, in this step reaction, select alkaline solutions such as ethylenediamine solution, the propylene diamine aqueous solution, the hexanediamine aqueous solution, diethylamine aqueous solution as extraction agent, concentration is between 10%-40%.Preferred ethylenediamine solution is between the concentration 20%-30%.
Extraction back Cefquinome and sulfuric acid reaction generate sulphuric acid cephalosporium quinol, use alcohol crystal, and the sulphuric acid cephalosporium quinol purity that obtains is good, and the yield height is an innovative point of the present invention.
Owing to adopted technical scheme as mentioned above, the present invention has following positively effect:
The present invention not only comprises Cefquinome, it is as wide spectrum, efficient, low toxicity, low residue animal specific microbiotic, directly serve the advantage of animal health industry aspect, but also has advantage after the technological innovation of Cefquinome technique for producing raw material, it just directly produces sulphuric acid cephalosporium quinol with the sulfuric acid salify without the hydroiodic acid HI Cefquinome, improve a lot on production cost and product purity, molar yield reaches more than 66.5%, and purity is more than 99%.
Embodiment one:
This prepares the method for sulphuric acid cephalosporium quinol, cefotaxime acid 115g is added among the methylene dichloride 2500ml, add tetrahydroquinoline 280ml, reacted 1 hour, and, collected extraction liquid with 25% ethylenediamine solution 500ml extraction three times, add gac 30g decolouring, add 2mol/l sulfuric acid and transfer pH to 1.3, reaction generates sulphuric acid cephalosporium quinol 106.9g (molar yield 67.6%, HPLC content 99.2%)
Embodiment two:
This prepares the method for sulphuric acid cephalosporium quinol, cefotaxime acid 115g is added among the methylene dichloride 2500ml ml, add tetrahydroquinoline 280ml, reacted 1 hour, and, collected extraction liquid with 30% propylene diamine aqueous solution 500ml extraction three times, add gac 30g decolouring, add 2mol/l sulfuric acid and transfer pH to 1.3, reaction generates sulphuric acid cephalosporium quinol 107.4g (molar yield 67.9%, HPLC content 99.3%).
Claims (4)
1. method for preparing sulphuric acid cephalosporium quinol, it is characterized in that: be the reaction of raw material and tetrahydroquinoline with the cefotaxime acid, after obtaining the product Cefquinome, through extraction, react in ethanolic soln with sulfuric acid behind the activated carbon decolorizing and obtain the final product sulphuric acid cephalosporium quinol, be i.e. (6R-7R)-7-[(2-amino-4-thiazolyl)-(methoxyimino) kharophen] 3-[(5,6,7, the 8-tetrahydric quinoline group) methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-vitriol;
Its chemical reaction equation process is:
2. the method for preparing sulphuric acid cephalosporium quinol according to claim 1, it is characterized in that: its concrete technical process is: cefotaxime acid is through Cefquinome, select for use suitable alkaline solution to make extraction agent, extraction back directly with sulfuric acid synthesize sulphuric acid cephalosporium quinol, in this step reaction, select alkaline solutions such as ethylenediamine solution, the propylene diamine aqueous solution, the hexanediamine aqueous solution, diethylamine aqueous solution as extraction agent, concentration is between 10%-40%; Preferred ethylenediamine solution is between the concentration 20%-30%; Extraction back Cefquinome and sulfuric acid reaction generate sulphuric acid cephalosporium quinol, use alcohol crystal, and the sulphuric acid cephalosporium quinol purity that obtains is good, the yield height.
3. the method for preparing sulphuric acid cephalosporium quinol according to claim 1, it is characterized in that: cefotaxime acid 115g is added among the methylene dichloride 2500ml, add tetrahydroquinoline 280ml, reacted 1 hour, and, collected extraction liquid with 25% ethylenediamine solution 500ml extraction three times, add gac 30g decolouring, add 2mol/l sulfuric acid and transfer pH to 1.3, reaction generates sulphuric acid cephalosporium quinol 106.9g (molar yield 67.6%, HPLC content 99.2%).
4. the method for preparing sulphuric acid cephalosporium quinol according to claim 1, it is characterized in that: cefotaxime acid 115g is added among the methylene dichloride 2500ml, add tetrahydroquinoline 280ml, reacted 1 hour, and, collected extraction liquid with 30% propylene diamine aqueous solution 500ml extraction three times, add gac 30g decolouring, add 2mol/l sulfuric acid and transfer pH to 1.3, reaction generates sulphuric acid cephalosporium quinol 107.4g (molar yield 67.9%, HPLC content 99.3%).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100484240A CN101108858A (en) | 2006-07-18 | 2006-07-18 | Method for preparing sulphuric acid cephalosporium quinol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100484240A CN101108858A (en) | 2006-07-18 | 2006-07-18 | Method for preparing sulphuric acid cephalosporium quinol |
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| Publication Number | Publication Date |
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| CN101108858A true CN101108858A (en) | 2008-01-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CNA2006100484240A Pending CN101108858A (en) | 2006-07-18 | 2006-07-18 | Method for preparing sulphuric acid cephalosporium quinol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103275103A (en) * | 2013-06-14 | 2013-09-04 | 河北科技大学 | Method for preparing cefquinome sulfate |
| JPWO2012147773A1 (en) * | 2011-04-28 | 2014-07-28 | 塩野義製薬株式会社 | Novel cephem compounds having catechol or pseudo-catechol structure |
-
2006
- 2006-07-18 CN CNA2006100484240A patent/CN101108858A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012147773A1 (en) * | 2011-04-28 | 2014-07-28 | 塩野義製薬株式会社 | Novel cephem compounds having catechol or pseudo-catechol structure |
| EP2703406A4 (en) * | 2011-04-28 | 2015-08-05 | Shionogi & Co | Novel cephem compound having catechol or pseudo-catechol structure |
| US9334289B2 (en) | 2011-04-28 | 2016-05-10 | Shionogi & Co., Ltd. | Cephem compound having catechol or pseudo-catechol structure |
| JP6006201B2 (en) * | 2011-04-28 | 2016-10-12 | 塩野義製薬株式会社 | Novel cephem compounds having catechol or pseudo-catechol structure |
| CN103275103A (en) * | 2013-06-14 | 2013-09-04 | 河北科技大学 | Method for preparing cefquinome sulfate |
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